Surface Functionalization Using Catalyst-Free Azide−Alkyne Cycloaddition

Citations Over TimeTop 1% of 2010 papers

Abstract

The utility of catalyst-free azide-alkyne [3 + 2] cycloaddition for the immobilization of a variety of molecules onto a solid surface and microbeads was demonstrated. In this process, the surfaces are derivatized with aza-dibenzocyclooctyne (ADIBO) for the immobilization of azide-tagged substrates via a copper-free click reaction. Alternatively, ADIBO-conjugated molecules are anchored to the azide-derivatized surface. Both immobilization techniques work well in aqueous solutions and show excellent kinetics under ambient conditions. We report an efficient synthesis of aza-dibenzocyclooctyne (ADIBO), thus far the most reactive cyclooctyne in cycloaddition to azides. We also describe convenient methods for the conjugation of ADIBO with a variety of molecules directly or via a PEG linker.

Related Papers

• → Synthesis of 1,2,3-Triazole-Fused Heterocycles via Intramolecular Azide-Alkyne Cycloaddition Reactions(2011)80 cited
• → Acetylene and Ethylene: Universal C2 Molecular Units in Cycloaddition Reactions(2021)27 cited
• → Cycloaddition reactions between dicyclohexylboron azide and alkynes(2013)23 cited
• → Palladium-catalyzed desymmetric [2+2+2] cycloaddition of 1,6-enyne and alkyne(2020)8 cited
• → Addition Reactions: Cycloaddition(2014)